EP0108720B1 - Ethers diallyliques cycloaliphatiques - Google Patents

Ethers diallyliques cycloaliphatiques Download PDF

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Publication number
EP0108720B1
EP0108720B1 EP19830810499 EP83810499A EP0108720B1 EP 0108720 B1 EP0108720 B1 EP 0108720B1 EP 19830810499 EP19830810499 EP 19830810499 EP 83810499 A EP83810499 A EP 83810499A EP 0108720 B1 EP0108720 B1 EP 0108720B1
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EP
European Patent Office
Prior art keywords
dicyclohexyl
diallyl
ether
mol
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP19830810499
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German (de)
English (en)
Other versions
EP0108720A1 (fr
Inventor
Charles E. Dr. Monnier
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
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Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0108720A1 publication Critical patent/EP0108720A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C43/188—Unsaturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic

Definitions

  • the present invention relates to diallyl ethers of 1,1'-dicyclohexanediols which are suitable for the preparation of the corresponding diglycidyl ethers by means of epoxidation.
  • the diglycidyl ethers of 1,1'-dicyclohexanediols are valuable epoxy resins insofar as they are characterized by a low viscosity and can therefore be used in particular as casting resins or reactive thinners.
  • the diglycidyl ether of 4,4'-dihydroxy-1,1'-dicyclohexyl is known from CH-A-476 787.
  • the invention thus relates to unsubstituted or alkyl-substituted diallyl ethers of the formula I. in which m and n each independently represent the number 1, 2 or 3, R and R 1 each independently represent an alkyl having 1-4 C atoms, the two allyl ether groups independently of one another in 1-, 2-, 3- , 4-, 5- or 6-position are bonded and wherein the alkyl group and the allyl ether group are not bonded to the same carbon atom.
  • the unsubstituted 2,2'-, 3,3'-, 4,4'-, 2,3'-, 3,4'- and 2,4'-diallyl ethers of the formula I are preferred compounds.
  • the compounds according to the invention can be prepared by using an unsubstituted or alkyl-substituted diol of the formula II wherein m, n, R and R 1 have the same meaning as in formula I, with allyl chloride or bromide to form the diallyl ether of formula I.
  • the diols of the formula II are partly known and partly new compounds.
  • diols of 1,1'-dicyclohexane can, for example, according to the in J. Am. Chem. Soc. 55, 4234-7 (1933) described processes can be obtained by hydrogenation of the corresponding biphenols, for example 2,2'-, 3,3'- or 4,4'-biphenol.
  • the reaction of the diols of 1,1'-dicyclohexane with allyl chloride or allyl bromide to give the diallyl ether of the formula I can be advantageously carried out, for example, by means of phase transfer catalysis in an alkaline medium and in the presence of a phase change catalyst. Such a method is described, for example, in EP application 046 731.
  • diallyl ethers of the formula I are not only valuable starting materials for the preparation of epoxy compounds by the epoxidation process, halogen-free epoxy resins being obtained in comparison with the production of epoxy resins by means of epichlorohydrin, but they are also valuable monomers which, alone or in a mixture with other polymerizable monomers, such as diallyl phthalate, triallyl cyanurate or styrene, can be converted into crosslinked polymers.
  • organic peracids such as peracetic acid, perpropionic acid, benzoperic acid, or also H 2 0 2 or hydroperoxides, such as tert-butyl hydroperoxide.
  • H 2 O 2 and organic acids such as formic acid, or preferably nitriles, such as benzonitrile or acetonitrile, or acid anhydrides, such as acetic anhydride or succinic anhydride, can also be used.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Ethers diallyliques non substitués ou porteurs d'un ou plusieurs radicaux alkyles, qui répondent à la formule 1 .
Figure imgb0005
dans laquelle m et n représentent chacun, indépendamment l'un de l'autre, un nombre égal à 1, à 2 ou à 3, R et R1 représentent chacun, indépendamment l'un de l'autre ou les uns des autres, un radical alkyle contenant de 1 à 4 atomes de carbone, les deux radicaux allyloxy se trouvent chacun, indépendamment l'un de l'autre, en l'une des positions 1, 2, 3, 4, 5, et 6, et le radical alkyle et le radical allyloxy ne se trouvent pas sur le même atome de carbone.
2. Ethers diallyliques de formule I selon la revendication 1 qui ne portent pas de substituants et dont les deux radicaux allyloxy se trouvent aux positions 2,2', 3,3', 4,4', 2,3', 3,4' et 2,4'.
3. Ether diallylique selon la revendication 1, en l'espèce le diallyloxy-4,4' bicyclohexyle-1,1'.
4. Ether diallylique selon la revendication 1, en l'espèce le diallyloxy-3,3' bicyclohexyle-1,1'.
EP19830810499 1982-11-04 1983-10-31 Ethers diallyliques cycloaliphatiques Expired EP0108720B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH641482 1982-11-04
CH6414/82 1982-11-04

Publications (2)

Publication Number Publication Date
EP0108720A1 EP0108720A1 (fr) 1984-05-16
EP0108720B1 true EP0108720B1 (fr) 1987-03-04

Family

ID=4309212

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19830810499 Expired EP0108720B1 (fr) 1982-11-04 1983-10-31 Ethers diallyliques cycloaliphatiques

Country Status (4)

Country Link
EP (1) EP0108720B1 (fr)
JP (1) JPS59231078A (fr)
CA (1) CA1243045A (fr)
DE (1) DE3369989D1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3919228A1 (de) * 1989-06-13 1990-12-20 Basf Ag Verfahren zur herstellung von di-(p-glycidoxicyclohexyl)-methan
JP4142155B2 (ja) * 1998-05-29 2008-08-27 ジャパンエポキシレジン株式会社 エポキシ樹脂及びその製造方法
JP2002128771A (ja) * 2000-10-26 2002-05-09 Sakamoto Yakuhin Kogyo Co Ltd 新規なエポキシ化合物の製造法、およびその方法で製造されたエポキシ化合物を含むエポキシ樹脂組成物
EP1270633B1 (fr) * 2001-06-25 2007-12-05 Mitsubishi Chemical Corporation Composés époxy alicycliques et leur procédé de production, composition de résine époxy alicyclique et encapsulant pour diode émettrice de lumière
JP2006188606A (ja) * 2005-01-06 2006-07-20 Nippon Steel Chem Co Ltd 新規エポキシ樹脂、その製造方法、エポキシ樹脂組成物及び硬化物
CN103003254B (zh) * 2010-07-14 2015-08-19 昭和电工株式会社 环氧化合物的制造方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH476787A (de) * 1965-07-10 1969-08-15 Ruetgerswerke Ag Verfahren zur Herstellung von lichtbogen- und kriechstrombeständigen Formkörpern oder Überzügen aus Kunstharzmassen
DE1643295A1 (de) * 1967-10-16 1971-07-01 Dow Chemical Co Verfahren zur Herstellung von Thiobisphenolaethern
US3927116A (en) * 1967-10-24 1975-12-16 Union Carbide Corp Bicyclo{8 2.2.1{9 {0 Hept-5(6)-yl compounds
GB1464287A (en) * 1974-02-22 1977-02-09 Ciba Geigy Ag Polymerisable esters
US4282353A (en) * 1978-11-30 1981-08-04 Ciba-Geigy Corporation Process for the preparation of unsaturated ketones containing glycidyl groups
US4342673A (en) * 1980-02-12 1982-08-03 General Electric Company High-solids coating compositions
US4304893A (en) * 1980-06-11 1981-12-08 Scientific Pharmaceuticals, Inc. 1,4-Bis[(3'-methacroyl-2'-hydroxypropoxy)methyl] cyclohexane

Also Published As

Publication number Publication date
JPS59231078A (ja) 1984-12-25
EP0108720A1 (fr) 1984-05-16
DE3369989D1 (en) 1987-04-09
CA1243045A (fr) 1988-10-11

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